Supramolecular Chemistry · NSF International REU

Regioselective Functionalization of Cyclodextrins

Studied selective deprotection and functionalization strategies for protected α-cyclodextrin derivatives during an NSF International REU project in Paris.

Cyclodextrin synthetic scheme — Enantiomeric α-cyclodextrin structures with modified primary rims.

Overview

This project explored regioselective functionalization of α-cyclodextrin, a cavitary molecule useful in supramolecular chemistry because its host–guest behavior and solubility can be tuned through chemical modification. The work focused on using selective debenzylation to access controlled spatial arrangements of primary alcohols on the cyclodextrin rim.

My role

I conducted this project through an NSF International REU at the Université Pierre et Marie Curie / Institut Parisien de Chimie Moléculaire in Paris, under the direction of Prof. Matthieu Sollogoub and Dr. Olivia Bistri. My work included synthesis, analytical sample preparation, characterization, and interpretation of selectively functionalized cyclodextrin derivatives.

Key outcomes

Studied selective deprotection of perbenzylated α-cyclodextrin to access new functionalization pathways.
Prepared cyclodextrin derivatives with controlled primary-rim substitution patterns.
Connected synthetic modification strategies to potential applications in metal-catalysis ligand design, enzyme mimicry, and chiral separation.
Presented the work through an ACS National Meeting abstract/presentation pathway.